I am convinced that something changes in men when their father dies.

We've all grown up in a culture that puts a heavy burden on the mantle of fatherhood, and the responsibility “the man of the house” is supposed to have. 

It doesn't matter what the quality of that relationship was. 

The loss of a father is the loss of the figure we expect to provide guidance, counsel, control, support. 

Or it’s the loss of the potential to have someone like that in our lives… the relationship we wish we had with our father. 

Well.

This week, one year ago, my dad died. 

He was a few days away from his 61st birthday. He never got to meet his first grandchild, who was born two months later.

His death was infuriatingly preventable. He died as a result of his own choices. He died very nearly broke. He died in agony. And he died alone. 

My relationship with him was strained when he passed. 

I had tried to stage something of an intervention in my mid-20s, talking to him about his pill and alcohol addictions — the things that shredded his liver and kidneys, killing him. 

He had also borrowed quite a bit of money from me (my life savings at the time) and not paid it back. He rarely reached out to me because, I am told, he was ashamed of this. 

As you can probably tell…

This Finance Daddy article will not be particularly uplifting. 

For me, it will be extremely vulnerable. 

I am hoping, however, that it will hold some instructive, hard truths for you.

The whole premise behind the “Finance Daddy” franchise is that too many people in America simply haven’t had a strong presence in their life to teach them how to build wealth. 

Part of this patriarchal theme comes from the fact that my father was a stock and option broker before becoming an entrepreneur… same as his father — my grandfather.

Both my father and grandfather got impressively rich very quickly. 

But both of them squandered their wealth by the end of their lives. 

My grandfather, a multimillionaire who once owned a mansion in Beverly Hills, died homeless, living at a friend’s house. My father was living in my grandmother’s guestroom the last few years of his life.

This issue will not be a eulogy for either elder MacIntyre. And what I share will not be particularly flattering.

I learned a great deal from both men…

My grandfather, for instance, taught me how to use a Bloomberg terminal to look up stock data in 1995, when I was 11 years old.

But I learned the most from their mistakes… The choices they made that financially ruined them and my family while I was growing up. 

Both men perfectly embodied the adage, "You can be a good example or a horrible warning." 

So let me share with you some of the things I learned from my father and his father… so that it might serve as a “horrible warning” to you. 

Lesson 1: Wall Street is Not Your Friend

If my dad had a big bill coming due, or needed money to make a mortgage payment, he would call his clients and invent some reason for them to sell out of their positions, or to buy options to “hedge” their portfolios so he could collect the commissions.

My grandfather would call up his clients and try to convince them to invest in penny stocks — so called “pump and dumps” — because the commissions were larger.

Stock brokers and investment advisors are, at their core, salesmen. 

And financial institutions, hedge funds, and brokerages are trying to sell you, too.

They want you to trade—to buy, to sell—because, traditionally, they don’t get paid if you make money… they get paid per transaction. 

And fee-free brokerages like Robinhood… they make money selling your order flow — your transactions. 

Even your 401(k) and other retirement plans are products — concocted, manufactured, and sold to businesses and consumers.

I’m not knocking salesmen. I am one myself. 

But I believe there’s ethical selling and unethical selling… Selling that’s mutually beneficial to both parties… Selling that’s transparent and honest and not trying to hide from or mislead the people being sold. 

And I feel that many people in the U.S. have been sold an idea without even realizing it… the idea that the stock market alone will make you rich. 

Of course, the financial industry — Wall Street —benefits if you have this notion. 

They’re the ones who get to profit regardless of whether you get rich or not.

So don’t fall into the trap. 

Investing in stocks and other financial products are just one facet of a broader wealth building strategy (see here for the full DIYwealth approach).

Lesson 2: Invest in What You Know

My grandfather, who was a millionaire by the time he was 30, bought a horse ranch in the 1970s. Turns out, raising racehorses is a vanity business — a vortex that sucks away your wealth. 

My father transitioned out of stock broking and briefly tried to work as a venture capitalist and investment banker. 

In the late 90s, he tried to raise money for a company called Electro K that sold plastic adhesive tabs that supposedly produced “negative ions” that would “heal the air” coming from electronic devices. A pseudoscientific scam, basically. 

Then he tried to launch and raise money for a car insurance bidding platform. I was never really clear on what this company did or why anyone would want to use it, and he could never really explain it without using a lot of buzzwords and jargon. 

Then he tried to launch his own employment and recruitment agency. 

In everything he did, he would always say he was a few months away from the big score, from making serious money…

Everything he did failed. Largely because he didn’t understand the businesses he was involved with. 

My dad had charm, charisma, and salesmanship. He had a superficial knowledge about a lot of things. 

But that only gets you so far in life. 

If you want to start a business or sell a service to a business…

You have to understand the particular manner that business makes money, and the market forces that impact that business. 

You need a deep knowledge that often only comes with diligence and extensive experience. Paying your dues and learning from your mistakes.

Usually this involves working for someone else — something my father said he could never do. 

Lesson 3: Don’t Squander What You Worked For

Both my dad and grandfather were stock brokers in the 1980s. Both of them loved to party. 

My grandmother hated The Wolf of Wall Street because of how much it reminded her of my grandfather. 

He would travel the world with my grandmother for months at a time — fancy hotels, expensive trips, the works. 

All that time and money he spent on leisure, he wasn’t working or making money. I’m told he would regularly go to casinos only to lose $50,000 in a single hand of blackjack. 

But wealth can be squandered even on a smaller scale...

I once, when I was 16 years old, added up the cost of my dad’s daily bar tabs as well as what he spent on alcohol at home in the course of a month. 

It was more than the mortgage payment. 

I had always wondered, growing up, how someone could earn nearly $400,000 in a year and still end up living paycheck to paycheck. I always wondered why my mom had to work three jobs to keep the house from getting foreclosed. 

As I got older, I realized that when someone makes a lot of money, very fast, they see it as permission to indulge themselves. 

They stop saying “no” to their vices. 

And they certainly don’t put money away for their future. 

So in this regard, a little bit of self-discipline goes a long way, especially as you begin to get wealthier. Prioritize your future and your family’s future, not your day-to-day desires, and you’ll be on the right path.

Lesson 4: Our Ambitions Can Keep Us From Having a Fulfilled Life or Healthy Relationships

When I think of my father, I think often about the ending of Arthur Miller’s “Death of a Salesman.” 

My father was Willy Loman to a T.

If you haven’t seen or read the play, “Death of a Salesman” is about an aging salesman who’s failed in his ambitions. 

He feels entitled to easy success and has delusions of being the hero to his family and envy of his friends… but he is constantly struggling financially. He’s constantly talking about the importance of popularity and being liked, but then he’s fired from his job. 

He blames everyone but himself for his failures, and he refuses to listen to anyone who tries to help or change his mind. 

“Death of a Salesman” is about generations of American men who heard the echoing call to succeed, to be “great”… only to wonder why they failed to live up to their own expectations. 

In the end, Loman has a confrontation with his eldest son, who rejects Loman’s aspirations, saying to his dad, “Will you take [your] phony dream and burn it before something happens?”

The dream, here, is synonymous with the American Dream.

Loman kills himself at the end of the play. He dies with grand ambitions for his son’s financial future.

Supposedly, after the play was first performed on Broadway in 1949, an entire row of grown men began to cry and could not stop crying. 

They pressed playbills to their face to hide their sobs.

They were taken to the hospital, and they were there, crying for hours. 

These grown, American men, who had survived the Great Depression and World War II — they could not stop crying. 

My dad, I think he wanted to be a good father. I think he wanted to be the man of the house. I think he wanted to do right by his family. 

Things don’t often turn out the way we intend.

Maybe he had the wrong dreams. Maybe he never knew who he was. 

Doesn’t matter. 

I wish he would have called me. 

I wish I had called him. 

I wish he could have met his grandchild. 

I wish we could have been men enough to bridge and repair the gap that had formed between us. 

But it’s too late for that. 

So it goes. 

If you have an estranged family member…

Someone you love who’s absent in your life…

Consider giving them a call. 

If you don’t try to mend that bridge now, you might never get the chance to do it again.

Next week, I promise we’ll get back to our regular commentary on wealth building and investing.

I swear it won’t be as depressing.